While talking to that friend of mine about his impending break-up, the question arose: What's the best way for someone to deliver the bad news in a situation like that?

A female pal of mine who got the ol' heave-ho recently thinks the worst line ever is, I don't think it's fair to you if we keep dating — the idea being that she seemed to want more out of the relationship than he did. "It just made me feel so pathetic — like I was so needy or something, or like I came off as desperate," she said.

That wouldn't necessarily be my read on the line — and I think, particularly in the case of a woman who wants to have a baby some day (as she does), the fairness explanation has plenty of validity. But it did make me wonder if there's any infallibly good way to go about it. I've been told in the past, "You're great, but I guess I'm not ready to be in a relationship right now" — which isn't the worst thing in the world to hear during the break-up conversation. But then you get over the thing by reminding yourself it wasn't about you as much as him not being ready for a relationship … which sometimes mean you dream of getting back together with him eventually ... only to hear, six months later, he's moved in with some chick. And then you're left to puzzle the whole thing out again and to find a new way of working through your distress.

So would it be better to simply say something like, "I think you're truly wonderful, but for whatever reason, I don't feel as connected to you as I'd like to be?"

I guess the thing is that it's never any fun to be rejected — and it's hard not to believe it's personal, rather than interpersonal. By that I mean: It's hard for many of us not to think, Oh, there's something wrong with me or I'm inferior in some way — that's why this didn't work out! But there are so many reasons that a relationship might not work out — reasons that have very little to do with who you are, and a lot to do with how the two of you interact, or even simply the dating market. (Which means that, for instance, single straight males in regions where they are vastly outnumbered by single straight females are a lot less interested in settling down than their counterparts in parts of the country where single straight chicks are more scarce.)

So … you know?

Nonetheless, if anyone has hit upon the perfect way to handle a break-up, please let the rest of us know.

What Do You Think?